Chicago’s 10 Best Mexican Restaurants

My original thought for a May-themed post was to talk about outdoor dining options, but anyone in Chicago right now can see that that’s just ridiculous thinking. It snowed a few days ago right after a 70-degree showing the day prior. But with Cinco de Mayo around the corner, these are my top 10 Mexican restaurants.

Flo has some of my favorite chilaquiles in the city without question. It’s not in the most popular part of the city, but the food will bring you over anyways. It’s a great option for Mexican brunch that doesn’t require you to wait too long or push over a pregnant woman while fighting for a table (not that I’d ever do that).

Many of my friends call Nuevo Leon their favorite spot. It’s probably the champion of tex-mex in Pilsen, one of the most heavily Mexican populated neighborhoods in town. There’s no flash or flare, just big plates of heavy-hitting flavors.

An excellent place to get cheap tacos and drinks. If you want something other than tacos, I’d go with the duck enchiladas. Opening a taco joint in Wicker Park leaves a restaurant open to the “it’s not Big Star” criticism. Well, I’d need to go a few more times before making that comparison, but my ranking speaks for itself. Antique Taco is a great spot to kick back and unbutton your pants.

My only suburban standout on the list. You’re more likely to sit next to a family with crying children, but it’s worth the risk. Chimichangas are my favorite Mexican dish, and although they call them Fried Burritos, they make ’em mean.

The only pricy option on my list, don’t go expecting any run-of-the-mill tacos or burritos. Rick Bayless makes his annual trip to Mexico to fill his saddle bag with ways to show off his take on the classics. The only catch is Frontera’s popularity makes it a real logistical nightmare to both get a reservation and to walk in.

This animated spot promises huge portions at minimal prices. Go with one of the whole fried red snappers or the skirt steak. Make a reservation, bring a huge group, and go crazy. The margaritas could use a bit more booze though, so be liberal when you order.

Who doesn’t love enjoying their taco among a sea of hipsters in a converted gas station? If you’re in the drinking mood, they always have a $3 whiskey shot, and Schlitz goes for $1. And if you’re not in the mood for a huge meal, the chips, guac, and pickled onions make for a great snack.

This garden-apartment-turned-insanely-popular-Mexican-restaurant has some of the best seasonal small plates in Lakeview. Make sure to bring a bottle of tequila or wine to have them make margaritas or sangria for you. The menu is anything but traditional, but you’ll be happy with the twists.

Brought to you by Chicago’s biggest name in the kitchen, Rick Bayless, this little sandwich shop brings creative flavors that hit home every time. The menu changes seasonally and has some killer sopas on it in case you don’t want a sandwich. The churros, soft serve, and hot chocolate make for some of the better Mexican desserts around, too. I’d suggest getting there early because the lines get loooooong.

These spicy sandwiches have kept me braving the drive west for some time now. With a toasted bun Chihuahua Cheese, and your choice of meat (I’d go with the Atomica or Al Pastor) you really can’t go wrong. Be forewarned that your clothes will stink like delicious Mexican food, so leave your jacket in the car. You can probably leave your wallet there too, since it’s so darn cheap.

Jeff Pearl has lived in the Chicagoland area his whole life, and is currently a medical student at Northwestern University’s Feinberg School of Medicine. Food has always been one of his passions. In his free time, Jeff enjoys cooking with his friends, going out to a new restaurant, or training for his next triathlon. In February 2010 he started writing about his dining experiences in his blog, Jeff Eats Chicago.